m-Chloroperbenzoic acid → 1-(N-benzyloxycarbonyl-N-phenylamino)-2,3-epoxypropane

HRID 1351850ノート

反応式

HRID 1351850 の反応式
[CH2:1]([N:4]([C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH:2]=[CH2:3].ClC1C=CC=C(C(OO)=[O:29])C=1.S([O-])(O)=O.[Na+]>ClCCl>[CH2:14]([O:13][C:11]([N:4]([CH2:1][CH:2]1[O:29][CH2:3]1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:12])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

参加物

5

反応物 3

HCID 70297m-Chloroperbenzoic acidHCID 11448535benzyl N-phenyl-N-(prop-2-en-1-yl)carbamateHCID 23665763Sodium Bisulfite

生成物 1

HCID 180073081-(N-benzyloxycarbonyl-N-phenylamino)-2,3-epoxypropane収率 37.7%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Under nitrogen, to a solution of N-allyl-N-phenyl-benzyloxycarbonylamine (5.5 g) in dichloromethane (50 ml) was added m-chloroperbenzoic acid (3.9 g) at 5° C., and the mixture was stirred at room temperature for 3 days. The resulting mixture was poured into aqueous sodium hydrogensulfite and extracted with ethyl acetate. The organic layer was successively washed with saturated aqueous sodium hydrogencarbonate and brine, dried over anhydrous magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=10:1 to 5:1) to give 1-(N-benzyloxycarbonyl-N-phenylamino)-2,3-epoxypropane (2.2 g).

後処理

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was successively washed with saturated aqueous sodium hydrogencarbonate and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=10:1 to 5:1)

出典と根拠

ORDレコード
ord-150d3487d6e641b299c8e750d1ae46a1
出典データセット
uspto-grants-2007_05
特許番号
US07217706B2

反応ノート

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